From the simplest Chuck Ts to shoes loaded with the symbolic weight of hip-hop appropriation, our sneakers say a lot about us. Beginning this month, some 140 pairs of iconic kicks, covering over a century of athletic footwear and ranging from the earliest proto–running shoe to the latest blinged-out Yeezys, are on display as the Oakland Museum of California hosts a first-of-its-kind traveling sneaker exhibition, Out of the Box: The Rise of Sneaker Culture(Dec. 22–Apr. 2). Evelyn Orantes, the museum’s curator of public practice, gave us a peek at a few highlights.

Reebok Freestyle, 1982 The Reebok Freestyle was one of the first athletic shoes geared directly to women, and also foreshadowed the broader trend toward weekend-warrior wear.

Converse Chuck Taylor All-Stars, 1917 Not long after basketball player and coach (and shoe salesman) Chuck Taylor started slinging his canvas-topped kicks, nearly every hoopster in the country was rocking a pair—making them perhaps the most important piece of footwear of all time.

Nike Air Jordan 1, 1985 His Airness was fined $5,000 per game for wearing his debut Nikes, which did not meet the NBA’s uniform code. When asked by David Letterman what rule the shoe violated, Jordan replied, “It doesn’t have any white in it.” To which Letterman quipped, “Well, neither does the NBA."

Pre-vulcanized rubber overshoe, circa 1830s The first rubber-soled shoes emerged in the mid-to-late 19th century in Brazil. However, because the shoes’ rubber wasn’t vulcanized, it wasn’t particularly durable. One nice element, however, was the customization potential: Intricate designs could be carved into the shoe by hand—literally, with one’s fingernail.

Vans checkerboard slip-on, 1977 The West Coast skater scene has also affected sneaker culture. Consider the Fast Times at Ridgemont High–era Vans, as much a part of SoCal fashion as business casual.